Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Pentafluorophenol is used in the preparation of pentafluorophenyl esters for peptide synthesis and vulcanized polymers. It is also used for peptide coupling and heterocyclic acid derivatives. It is involved in the preparation of pentafluorophenyl formate which acts as a formulating agent for amines and amino acids.
Solubility
Soluble in water.
Notes
Moisture sensitive. Incompatible with strong oxidizing agents, bases, acid chlorides and acid anhydrides.
RUO – Research Use Only
General References:
- Widely used for peptide coupling (see Appendix 6) via the active PFP esters, generally prepared by carbodiimide coupling: Liebigs Ann. Chem., 1421 (1973); Tetrahedron Lett., 1785 (1974). With Fmoc-protected amino acids, the coupling takes place very rapidly, which reduces the amount of Fmoc-cleavage during the peptide bond formation: Synthesis, 325 (1983). Fmoc protected PFP esters have also been applied in solid phase peptide synthesis: Tetrahedron, 44, 843 (1988). PFP esters have been recommended for preparation of derivatives of heterocyclic acids, effective where DCC or DIC alone fail: Synth. Commun., 28, 753 (1998).
- For preparation and use of the moderately stable PFP formate as a formylating agent for amines and amino acids, see: Synthesis, 510 (1987).
- Pandith, A.; Kumar, A.; Kim, H. S. 9-N-Alkylaminomethylanthracene probes for selective fluorescence sensing of pentafluorophenol. RSC Adv. 2015, 5 (100), 81808-81816.
- Alonso, J. M.; Fabre, B.; Trilling, A. K.; Scheres, L.; Franssen, M. C.; Zuilhof, H. Covalent Attachment of 1-Alkenes to Oxidized Platinum Surfaces. Langmuir. 2015, 31 (9), 2714-2721.